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Acetic Acid → {4-[4-(2-Isopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 2377798
Notes
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Reaction equation

HRID 2377798 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O.[CH:34]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)([CH3:36])[CH3:35]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([N:47]2[CH2:48][CH2:49][CH:44]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[O:37][CH:34]([CH3:36])[CH3:35])[CH2:45][CH2:46]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 105368744-(2-Isopropoxyphenyl)piperidine

Product 1

HCID 58712706{4-[4-(2-Isopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-carbamic acid tert-butyl esterYield 48%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

A (4-oxo-cyclohexyl)-carbamic acid tert-butyl ester Compound 1b (1.54 g, 7.21 mmol), NaBH(OAc)3 (64.45 g, 21.0 mmol) and HOAc (0.3 mL) were added to a solution of 4-(2-isopropoxy-phenyl)-piperidine Compound 1a (1.32 g, 6.01 mmol) in CH2Cl2 (100 mL). The mixture was stirred under N2 for two days, then the reaction was quenched with MeOH. The mixture was evaporated and the resulting residue was redissolved with CH2Cl2, washed using 10% aqueous Na2CO3 and brine, then dried (Na2SO4). The crude product was purified by column chromatography to provide {4-[4-(2-isopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-carbamic acid tert-butyl ester Compound 1c as a mixture of cis/trans isomers (MS 416; yellowish oil; 1.19 g, 48% yield).

Workup

  1. customthe reaction was quenched with MeOH
  2. customThe mixture was evaporated
  3. dissolutionthe resulting residue was redissolved with CH2Cl2
  4. washwashed
  5. dry with materialdried (Na2SO4)
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ae5e799bd3b544039e270fad6db9d4dd
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07470711B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes