Sodium triacetoxyborohydride → HCID 66772180, compound

HRID 1887528Notes

Reaction equation

HRID 1887528 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.O=[CH:13][CH2:14][C:15]1[C:23]2[C:22]([C:24]([O:26][CH3:27])=[O:25])=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl>[C:31]1([S:28]([N:17]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[C:23]=3[C:15]([CH2:14][CH2:13][NH:3][C@H:4]3[CH:9]4[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]4)[CH2:5]3)=[CH:16]2)(=[O:29])=[O:30])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochlorideHCID 15240968HCID 15240968, compound

Product 1

HCID 66772180HCID 66772180, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-(−)-3-aminoquinuclidine dihydrochloride (202 mg, 1.01 mmol) and methyl 3-(2-oxoethyl)-1-(phenylsulfonyl)-1H-indole-4-carboxylate (330 mg, 0.92 mmol) from Step C above in 1% acetic acid in dichloromethane (20 mL) was stirred at ambient temperature for 16 h. Sodium triacetoxyborohydride (584 mg, 2.76 mmol) was added, and the resulting suspension was stirred for 2 h at ambient temperature. The solvent was removed under reduced pressure, and the crude material purified by column chromatography (silica gel, 10:1:0.1 dichloromethane/methanol/concentrated ammonium hydroxide) to afford (S)-methyl 1-(phenylsulfonyl)-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indole-4-carboxylate (172 mg, 40%) as a yellow oil: MS (ESI+) m/z 468 (M+H).

Workup

  1. stirringthe resulting suspension was stirred for 2 h at ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe crude material purified by column chromatography (silica gel, 10:1:0.1 dichloromethane/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-2fba79715a564d608a3f18b5c0319818
Source dataset
uspto-grants-2013_08
Patent number
US08501729B2

Reaction notes

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