Piperidine → HCID 11307659, compound

HRID 747064Notes

Reaction equation

HRID 747064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][C:13](=[O:17])[C@H:12]2[CH2:18][C:19]([NH:21][C@H:22]2[C:31]3[C:26](=[CH:27][C:28]([CH2:32][CH:33]=O)=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][C:13](=[O:17])[C@H:12]2[CH2:18][C:19]([NH:21][C@H:22]2[C:31]3[C:26](=[CH:27][C:28]([CH2:32][CH2:33][N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86596033HCID 86596033, compound

Product 1

HCID 11307659HCID 11307659, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from step E (63 mg, 0.116 mmol) and piperidine (20 mg, 0.23 mmol) in 1 mL of dichloroethane was added sodium triacetoxyborohydride (49 mg, 0.23 mmol). After stirring overnight at room temperature, the reaction solution was diluted with EtOAc and washed with sat. NaHCO3 and brine. The organic phase was dried over Na2SO4 and evaporated to dryness in vaco. Flash chromatography (SiO2, EtOAc to EtOAc/MeOH=100:10 to 100:12) afforded the title compound as a white solid. MS: 573.2 (M+1).

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated to dryness in vaco

Sources & evidence

ORD record
ord-79840d2ae7e24194a0efc4e22ec4567f
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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