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

HRID 1272157Notes

Reaction equation

C(OC(N1C[C@@H](C)N2[C@H](CC3C2=NC(C(F)F)=C(CO)C=3)C1)=O)(C)(C)C.[C:27]([O:31][C:32]([N:34]1[CH2:46][C@@H:45]([CH3:47])[N:44]2[C@H:36]([CH2:37][C:38]3[C:43]2=[N:42][C:41]([C@H:48]([O:50][CH3:51])[CH3:49])=[C:40]([CH:52]=[O:53])[CH:39]=3)[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].[BH4-].[Na+]>>[C:27]([O:31][C:32]([N:34]1[CH2:46][C@@H:45]([CH3:47])[N:44]2[C@H:36]([CH2:37][C:38]3[C:43]2=[N:42][C:41]([C@H:48]([O:50][CH3:51])[CH3:49])=[C:40]([CH2:52][OH:53])[CH:39]=3)[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

Reactant 3

HCID 4311764Sodium borohydride

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

HCID 86596363(4R,9aR)-7-formyl-6-(1-(R)-methoxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 69360410(4R,9aR)-7-hydroxymethyl-6-(1-(R)-methoxy-ethyl)-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)-7-formyl-6-(1-(R)-methoxy-ethyl)-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-7193734c8b5144568f2a02d7b7803172
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208494B2

Reaction notes

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