Sodium borohydride → (4R,9aR)-6-difluoromethyl-7-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 1272140Notes

Reaction equation

C(OC(N1C[C@@H](C)N2[C@H](CC3C2=NC(CC)=C(CO)C=3)C1)=O)(C)(C)C.[C:26]([O:30][C:31]([N:33]1[CH2:45][C@@H:44]([CH3:46])[N:43]2[C@H:35]([CH2:36][C:37]3[C:42]2=[N:41][C:40]([CH:47]([F:49])[F:48])=[C:39]([CH:50]=[O:51])[CH:38]=3)[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].[BH4-].[Na+]>>[C:26]([O:30][C:31]([N:33]1[CH2:45][C@@H:44]([CH3:46])[N:43]2[C@H:35]([CH2:36][C:37]3[C:42]2=[N:41][C:40]([CH:47]([F:49])[F:48])=[C:39]([CH2:50][OH:51])[CH:38]=3)[CH2:34]1)=[O:32])([CH3:27])([CH3:28])[CH3:29]

Participants

Reactant 3

HCID 4311764Sodium borohydride

HCID 69359485(4R,9aR)-6-ethyl-7-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HCID 86596362(4R,9aR)-6-difluoromethyl-7-formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 69360356(4R,9aR)-6-difluoromethyl-7-hydroxymethyl-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 15, intermediate b) from (4R,9aR)-6-difluoromethyl-7-formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester and sodium borohydride.

Sources & evidence

ORD record: ord-1161ecd1d480451eacb8bf47cc6a520a
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208494B2

Reaction notes

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