Diisopropylethylamine → HCID 70158604, compound

HRID 2301758Notes

Reaction equation

HRID 2301758 reaction equation
[CH3:1][N:2]([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)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4].[ClH:25].[CH2:26]([O:33][C:34]([N:36]([CH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH2:37][CH3:38])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[ClH:25].[CH3:1][N:2]([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:42]2[CH2:43][CH2:44][CH:39]([N:36]([C:34]([O:33][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:35])[CH2:37][CH3:38])[CH2:40][CH2:41]2)[CH2:13]1)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18677675HCID 18677675, compoundHCID 88116399HCID 88116399, compound

Product 1

HCID 70158604HCID 70158604, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-(RS)-(N-(methyl)-N-(phenylsulfonyl)amino)-3-(SR)-(formyl)-4-(SR)-phenylcyclopentane (from Step D, derived from Higher Rf isomer in Step C) (10 mg, 0.029 mmol) (from Step F) in 1,2-dichloroethane (1 mL) was added 4-(N-(benzyloxycarbonyl)-N-(ethyl)amino)piperidine hydrochloride (18 mg, 0.058 mmol) and DIPEA (0.010 mL, 0.058 mmol). After 15 min, sodium triacetoxyborohydride (19 mg, 0.087 mmol) was added and the reaction was stirred at RT for 4-16 h. The reaction was evaporated under nitrogen, quenched with aq. sodium carbonate and extracted 3 times with ethyl acetate. The organic layers were each washed with brine, dried over sodium sulfate, combined and concentrated in vacuo. The residue was purified by Prep TLC eluting with 2-5% methanol in methylene chloride to give the title product (17 mg) as the free amine. The hydrochloride salt was prepared by taking up the free amine in ether, addition of excess 1M hydrogen chloride in ether and evaporation to dryness to afford the title compound usually as a white solid.

Workup

  1. customThe reaction was evaporated under nitrogen
  2. customquenched with aq. sodium carbonate
  3. extractionextracted 3 times with ethyl acetate
  4. washeach washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Prep TLC
  8. washeluting with 2-5% methanol in methylene chloride

Sources & evidence

ORD record
ord-313e8835606f4fa4818058c61e94103c
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

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