Sodium borohydride → (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

HRID 1272133Notes

Reaction equation

C(OC(N1C[C@@H](C)N2[C@H](CC3C2=NC(C)=C(CO)C=3)C1)=O)(C)(C)C.[C:25]([O:29][C:30]([N:32]1[CH2:44][C@@H:43]([CH3:45])[N:42]2[C@H:34]([CH2:35][C:36]3[C:41]2=[N:40][C:39]([CH2:46][CH3:47])=[C:38]([CH:48]=[O:49])[CH:37]=3)[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[BH4-].[Na+]>>[C:25]([O:29][C:30]([N:32]1[CH2:44][C@@H:43]([CH3:45])[N:42]2[C@H:34]([CH2:35][C:36]3[C:41]2=[N:40][C:39]([CH2:46][CH3:47])=[C:38]([CH2:48][OH:49])[CH:37]=3)[CH2:33]1)=[O:31])([CH3:26])([CH3:27])[CH3:28]

Participants

Reactant 3

HCID 4311764Sodium borohydride

HCID 69358194(4R,9aR)-7-hydroxymethyl-4,6-dimethyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HCID 86596360(4R,9aR)-6-ethyl-7-formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

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

Procedure

This compound was prepared in analogy to example 15 intermediate b), from (4R,9aR)-6-ethyl-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-7570f76becc547238aa3009872800c4b
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208494B2

Reaction notes

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