Acetic Acid → HCID 69557956, compound

HRID 1862716Notes

Reaction equation

HRID 1862716 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:16][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]([CH:23]=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([CH2:31][CH2:32][CH2:33][CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:16][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]([CH2:23][N:37]2[CH2:38][CH2:39][CH:34]([CH2:33][CH2:32][CH2:31][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:35][CH2:36]2)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 876784-(3-Phenylpropyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 87888818HCID 87888818, compound

Product 1

HCID 69557956HCID 69557956, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-((SR)-(benzyloxycarbonylamino)-3-(SR)-(formyl)-4-(SR)-phenylcyclopentane (from Step F, derived from Higher Rf isomer in Step D) (450 mg, 0.1.4 mmol) in 1,2-dichloroethane (10 mL) was added 4-(3-phenylprop-1-yl)piperidine (424 mg, 2.1 mmol) and acetic acid (0.125 mL, 2.1 mmol). After 15 min, sodium triacetoxyborohydride (890 mg, 4.2 mmol) was added in portions over 30 min and the reaction was stirred at RT for 16 h. The reaction was diluted with methylene chloride, quenched with aq. sodium carbonate and extracted 3 times with methylene chloride. The organic layers were each washed with brine, dried over sodium sulfate, combined and concentrated in vacuo. The residue was purified by FC (30-40% ethyl acetate in hexanes) to give the title product (698 mg) as the free amine.

Workup

  1. customquenched with aq. sodium carbonate
  2. extractionextracted 3 times with methylene chloride
  3. washeach washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by FC (30-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e0057d364f524284a22b9f4aeb606d9c
Source dataset
uspto-grants-2003_03
Patent number
US06538002B1

Reaction notes

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