Acetic Acid → HCID 69422567, compound

HRID 1178870Notes

Reaction equation

HRID 1178870 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20]([CH2:22][NH:23][CH:24]1[CH2:28][CH2:27][C:26](=O)[CH2:25]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[CH3:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(O)(=O)C.[OH-].[Na+].[ClH:43].C(OCC)C>ClCCCl>[ClH:43].[C:15]([O:19][C:20]([CH2:22][NH:23][C@H:24]1[CH2:28][CH2:27][C@@H:26]([N:34]2[CH2:35][CH2:36][CH:31]([CH3:30])[CH2:32][CH2:33]2)[CH2:25]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

9

Reactant 7

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 693814-MethylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 69419650HCID 69419650, compound

Product 1

HCID 69422567HCID 69422567, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (3.37 g, 15.9 mmol) was added to a solution of 3-[(tert-butyloxycarbonyl)methylamino]cyclopentan-1-one (2.42 g, 11.3 mmol), 4-methylpiperidine (1.2 ml, 10 mmol) and acetic acid (0.65 ml, 11 mmol) in 1,2-dichloroethane (40 ml). The resulting mixture was stirred at room temperature overnight (22 h). 1M Aqueous sodium hydroxide (100 ml) was added and the mixture extracted with dichloromethane (2×40 ml). The combined extracts were dried (MgSO4) and evaporated. The residue was dissolved in diethyl ether (40 ml) and treated with 1M hydrogen chloride in diethyl ether (10 ml, 10 mmol) to give a precipitate. The solid was collected under suction, washed with diethyl ether then isohexane and dried in vacuo (2.89 g). A portion of this solid (1.764 g) was recrystallized from methanol-ethyl acetate to afford the title product (0.7203 g, 35%) as a white solid; δH (400 MHz, CD3OD) 1.02 (3H, d, J 6.7 Hz), 1.39-1.41 (2H, m), 1.46 (9H, s), 1.71 (1H, m), 1.83-1.98 (6H, m), 2.14 (1H, m), 2.27 (1H, m), 2.82 (3H, s), 2.93 (2H, m), 3.50 (1H, m), 3.59 (2H, m), 4.44 (1H, m); m/z (ES+) 297 ([M+H]+), 241 (100%).

Workup

  1. extractionthe mixture extracted with dichloromethane (2×40 ml)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. dissolutionThe residue was dissolved in diethyl ether (40 ml)
  5. customto give a precipitate
  6. customThe solid was collected under suction
  7. washwashed with diethyl ether
  8. dry with materialisohexane and dried in vacuo (2.89 g)
  9. customA portion of this solid (1.764 g) was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-3218d29cee3b4a398cdbc484af86ffe5
Source dataset
uspto-grants-2007_10
Patent number
US07276607B2

Reaction notes

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