Sodium triacetoxyborohydride → (1R)-1-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl][6-(4-phenylbutoxy)hexyl]amino}ethanol

HRID 1072959Notes

Reaction equation

HRID 1072959 reaction equation
[CH3:1][C:2]1([CH3:25])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:24])[CH2:13][NH:14][C@@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][OH:17])=[CH:11][C:5]=2[CH2:4][O:3]1.[C:26]1([CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH:42]=O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:25])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:24])[CH2:13][N:14]([C@@H:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:16][OH:17])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][CH2:33][CH2:32][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11163708(1R)-1-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethanolHCID 113686626-(4-Phenylbutoxy)hexanal

Product 1

HCID 10120860(1R)-1-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl][6-(4-phenylbutoxy)hexyl]amino}ethanolYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cloudy mixture of (1R)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethanol (500 mg) and crude 6-(4-phenylbutoxy)hexanal (400 mg) in CH2Cl2 (3 ml) under nitrogen was added sodium triacetoxyborohydride (433 mg) in one portion. A gelatinous mixture formed initially which thinned over a 15 min period. The resulting light yellow solution was stirred for 18 h before it was partitioned between ethyl acetate (10 ml) and saturated aqueous NaHCO3 (30 ml). The aqueous layer was extracted with ethyl acetate (3×20 ml) and the combined organic layers were dried (MgSO4) and concentrated in vacuo to give the title compound (725 mg).

Workup

  1. customA gelatinous mixture formed initially which thinned over a 15 min period
  2. customwas partitioned between ethyl acetate (10 ml) and saturated aqueous NaHCO3 (30 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×20 ml)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86ecf7a1ffda45f99b470568fed00223
Source dataset
uspto-grants-2005_06
Patent number
US06911560B2

Reaction notes

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