Sodium borohydride → (2R,4S)-2-benzyl-1-(9-fluorenoyl)-N-(4-quinolylmethyl)-4-piperidinamine

HRID 264668Notes

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]([CH:34]1[C:46]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[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]([CH:34]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=2[C:41]2[C:46]1=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 57193281(2R*,4S*)-2-Benzyl-1-(9-fluorenoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57207891(2R*,4S*)-2-benzyl-1-(9-fluorenoyl)-N-(4-quinolylmethyl)-4-piperidinamine

Procedure

0.238 g (0.384 mmol) of (2R*,4S*)-2-benzyl-1-(9-fluorenoyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine is reacted with 0.066 g (1.54 mmol) of sodium borohydride in analogy to Example 2. The title compound ##STR70## is obtained (0.155 g, 79%) as white foam. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.36, FD-MS: M+ =523.

Sources & evidence

ORD record: ord-5c4f4a9d5cdd4a56bd1ad6333893a023
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646144

Reaction notes

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