Sodium triacetoxyborohydride → HCID 53815656, compound

HRID 1599444Notes

Reaction equation

HRID 1599444 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]1([CH:21]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:22]2[C@@H:27]([NH2:28])[CH:26]3[CH2:29][CH2:30][N:23]2[CH2:24][CH2:25]3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:37][O:38][C:39]([C:42]1[CH:43]=[CH:44][C:45]([O:50][CH3:51])=[C:46]([CH:49]=1)[CH:47]=O)([CH3:41])[CH3:40]>C(Cl)Cl>[CH3:51][O:50][C:45]1[CH:44]=[CH:43][C:42]([C:39]([O:38][CH3:37])([CH3:40])[CH3:41])=[CH:49][C:46]=1[CH2:47][NH:28][C@H:27]1[CH:26]2[CH2:29][CH2:30][N:23]([CH2:24][CH2:25]2)[C@H:22]1[CH:21]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12225560HCID 12225560, compoundHCID 18928645HCID 18928645, compound

Product 1

HCID 53815656HCID 53815656, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (152 mg, 0.707 mmol) was added to a solution of (2S,3S)-2-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-amine(135 mg, 0.462 mmol) and 5-(1-methoxy-1-methylethyl)-2-methoxybenzaldehyde prepared in example 1 (92 mg, 0.442 mmol) dissolved in methylene chloride (4 ml) at room temerature, and the resulting solution was stirred for 4 h. The reaction mixture was diluted with methylene chloride, and washed with aq. sodium bicarbonate solution and brine. The extracts were dried over magnesium sulfate, and concentrated by evaporation. The residual oil was purified by crystallization from methylene chloride to yield analytically pure sample of the title compound as a white crystal (94 mg, 42%).

Workup

  1. washwashed with aq. sodium bicarbonate solution and brine
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residual oil was purified by crystallization from methylene chloride

Sources & evidence

ORD record
ord-bec75b0e4a6b4adb894992e3fa0007b8
Source dataset
uspto-grants-1998_04
Patent number
US05741797

Reaction notes

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