Piperidine → HCID 9894504, compound

HRID 1269452Notes

Reaction equation

HRID 1269452 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([NH:13][C:14](=[O:35])[CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]3[S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)(=[O:24])=[O:23])[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1)=O.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN(C)C(=O)C>[N:36]1([CH2:1][C:3]2[CH:12]=[C:11]3[C:6]([C@H:7]([NH:13][C:14](=[O:35])[CH2:15][CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][N:17]4[S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:32])[F:34])[CH:26]=4)(=[O:24])=[O:23])[CH2:8][CH2:9][O:10]3)=[CH:5][CH:4]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 18448669HCID 18448669, compound

Product 1

HCID 9894504HCID 9894504, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(7-Formyl-chroman-4-(R)-yl)-2-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-2-yl]-acetamide (135 mg, 0.26 mmol) and piperidine (28 mg, 0.33 mmol) were added to N,N-dimethyl-acetamide (1.5 mL) solution, followed by NaBH(OAc)3 (115 mg, 0.52 mmol) and the reaction was stirred overnight (14 h). The reaction was quenched with dilute NaHCO3—H2O (10 mL), and the mixture was extracted with CH2Cl2 (2×10 mL), and the organic phase was washed with dilute NaHCO3—H2O and H2O, and dried over MgSO4. After filtration and concentration in vacuo, the crude was purified by precipitation and crystallization as the HCl salt in Et2O to provide a white solid (of the title compound as a mixture of diastereomers (ca. 1:1 by 1H NMR). MS (ESI) 580 (M+H)+.

Workup

  1. customThe reaction was quenched with dilute NaHCO3—H2O (10 mL)
  2. extractionthe mixture was extracted with CH2Cl2 (2×10 mL)
  3. washthe organic phase was washed with dilute NaHCO3—H2O and H2O
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and concentration in vacuo
  6. customthe crude was purified by precipitation and crystallization as the HCl salt in Et2O

Sources & evidence

ORD record
ord-7cb3ca5462e54b76a9ca3fa786d00e3c
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

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