1-Benzyl-3-hydroxy-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester → (5 SR,6RS)-8-benzyl-6-hydroxy-2-[4-((rac)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one

HRID 1260492Notes

Reaction equation

HRID 1260492 reaction equation
C(O[C:4]([C:6]1([CH2:20][CH2:21]OC)[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH:7]1[OH:19])=[O:5])C.[F:24][C:25]([F:37])([F:36])[CH:26]([CH3:35])[O:27][C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1>>[CH2:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:5])[N:34]([C:31]3[CH:32]=[CH:33][C:28]([O:27][CH:26]([CH3:35])[C:25]([F:24])([F:36])[F:37])=[CH:29][CH:30]=3)[CH2:21][CH2:20]2)[CH:7]([OH:19])[CH2:8]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 580566191-Benzyl-3-hydroxy-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl esterHCID 662775684-(2,2,2-Trifluoro-1-methyl-ethoxy)-aniline

Product 1

HCID 58056626(5 SR,6RS)-8-benzyl-6-hydroxy-2-[4-((rac)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one

Procedure

The title compound was prepared in analogy to example 1 step C from a mixture of (3RS,4SR)-1-benzyl-3-hydroxy-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester and (rac)-4-(2,2,2-trifluoro-1-methyl-ethoxy)-phenylamine. Light yellow solid. MS (ESI): 449.2 (MH+)

Sources & evidence

ORD record
ord-5ecf3fda1fec45dbb584db2737ac3fa3
Source dataset
uspto-grants-2013_06
Patent number
US08470843B2

Reaction notes

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