Sodium borohydride → HCID 56987150, compound

HRID 264645Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([N:14]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)C(=O)C(F)(F)F)[CH2:11][CH2:10][N:9]1[C:32]([C@H:34]1[NH:46][CH2:45][C:37]2[NH:38][C:39]3[C:44]([C:36]=2[CH2:35]1)=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[CH2:11][CH2:10][N:9]1[C:32]([C@H:34]1[NH:46][CH2:45][C:37]2[NH:38][C:39]3[C:44]([C:36]=2[CH2:35]1)=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 57245952HCID 57245952, compound

Product 1

HCID 56987150HCID 56987150, compound

Procedure

197 mg (0.3 15 mmol) of the mixture of (2R*,4S*)-2-benzyl-1-((3S)-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-3-yl)carbonyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine diastereomers are reacted with 48 mg (1.26 mmol) of sodium borohydride in analogy to Example 2. The title compound ##STR47## is obtained as mixture of diastereomers in the form of white foam. TLC: methylene chloride/methanol/conc. ammonia (350:50:1) Rf =0.50, FD-MS: M+ =529.

Sources & evidence

ORD record: ord-9b188aafca0a4ceabb39bb081af5262d
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646144

Reaction notes

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