Sodium cyanoborohydride → (4R,9aS)-6-Bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic Acid tert-butyl Ester

HRID 11914Notes

Reaction equation

ClC1N=C2C(=CC=1)C=C1N2[C@H](C)CNC1=O.[C:17]([O:21][C:22]([N:24]1[CH2:36][C@@H:35]([CH3:37])[N:34]2[C:26](=[CH:27][C:28]3[C:33]2=[N:32][C:31]([Br:38])=[CH:30][CH:29]=3)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C([BH3-])#N.[Na+]>>[C:17]([O:21][C:22]([N:24]1[CH2:36][C@@H:35]([CH3:37])[N:34]2[C@@H:26]([CH2:27][C:28]3[C:33]2=[N:32][C:31]([Br:38])=[CH:30][CH:29]=3)[CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

Reactant 3

HCID 5003444Sodium cyanoborohydride

HCID 86590110(R)-6-chloro-4-methyl-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one

HCID 86590112(4R)-6-bromo-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 86590111(4R,9aS)-6-Bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic Acid tert-butyl Ester

Procedure

This compound was prepared in analogy to Example 2, intermediate b) from (R)-6-bromo-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester and sodium cyano borohydride.

Sources & evidence

ORD record: ord-9e857f4086cd4f5592763c9b4669cb23
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098337B2

Reaction notes

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