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B11OS > Synthesis of Indoles (protecting groups) > Flashcards

Synthesis of Indoles (protecting groups) Flashcards

1
Q

DMF-DMA

A

protected aldehyde

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2
Q

TiCl3

A

reduces nitro group and produces HCl to hydrolyse enamine

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3
Q

Remove OBn protecting group

A

hydrogenation gives OH

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4
Q

Uses of hydrogenation

A

OBn to OH
nitro to amino
nitrile to imine

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5
Q

Remove trifluoro acetal group

A

0.1M HCl in Et2O

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6
Q

remove -OTMs

A

aqueous acid

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7
Q

remove -NRTMs

A

aqueous acid

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8
Q

Fishcer indole products

A

symmetrical aldehydes/ketones give one product
unsymmetrical aldehydes/ketones give mixture of products

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9
Q

Add/remove MOM

A

add - MeOCH2Cl
remove - acid labile

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10
Q

Add/remove SEM

A

add - ClCH2O(CH2)2SiEt3
remove - fluoride labile

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11
Q

add/remove phenylsulfonyl

A

add - Ph2SO2Cl
remove - base labile

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12
Q

add/remove Boc

A

add - Boc2O
remove - acid labile

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13
Q

add/remove urea

A

add - tBuNCO
remove - base labile

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B11OS (10 decks)

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