Dichloromethane → HCID 18666869, compound

HRID 356631Notes

Reaction equation

HRID 356631 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[C:9]([CH:10]=O)[C:8]([O:13][CH3:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:15][C@@H:16]1[C@H:21]([CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:20]2[CH2:35][CH2:36][C@H:17]1[C@@H:18]([C:37]([NH2:39])=[O:38])[CH2:19]2.C(Cl)[Cl:41]>>[ClH:41].[ClH:41].[C:29]1([CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:21]2[N:20]3[CH2:35][CH2:36][C@@H:17]([C@@H:18]([C:37]([NH2:39])=[O:38])[CH2:19]3)[C@@H:16]2[NH:15][CH2:10][C:9]2[CH:12]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=[CH:7][C:8]=2[O:13][CH3:14])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 1893897455845-76-6HCID 57164149HCID 57164149, compound

Product 1

HCID 18666869HCID 18666869, compoundYield 58.2%

Procedure

A mixture of 5-methylsulfonyl-o-anisaldehyde (364 mg,1.7 mmol), (3R,4S,5S,6S)-5-amino-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxamide (500 mg, 1.50 mmol) and NaBH(Oac)3 (636 mg, 3.0 mmol) in CH2Cl2 (10 ml) was stirred at room temperature for 3 hr. The reaction mixture was extracted with CH2Cl2 (300 ml), washed with NaHCO3 aqueous solution and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography. The resulted product was diluted with HCl/methanol (15 ml), stirred for 30 min and the white precipitate (appeared during the reaction) was collected by filtration to afford a titled compound (589 mg, 58.2%) as a white crystalline.

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2 (300 ml)
  2. washwashed with NaHCO3 aqueous solution and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. additionThe resulted product was diluted with HCl/methanol (15 ml)
  7. stirringstirred for 30 min
  8. customthe white precipitate (appeared during the reaction)
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1b6143fdbae3431bad8fd8912f327340
Source dataset
uspto-grants-1998_11
Patent number
US05837711

Reaction notes

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