Isopropanol → HCID 57512964, compound

HRID 1350998Notes

Reaction equation

HRID 1350998 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C@H:17]2[CH2:19][O:18]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H:28]1([NH2:38])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)CCC1.[CH:39]([OH:42])(C)C>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C@H:17]([OH:18])[CH2:19][NH:38][CH2:28][C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([O:42][CH3:39])[CH:32]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 2761804HCID 2761804, compoundHCID 70580741-Aminotetralin, (S)-

Product 1

HCID 57512964HCID 57512964, compound

Conditions

Temperature
90 °C

Procedure

A mixture of tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate (V, 1.58 g, 4.28 mmol) and 3-methoxybenzylamine (VI, 825 microliter, 6.42 mmol) in isopropanol (45 mL) is heated to 90 degrees C. for 4 hours. Upon cooling to 20–25 degrees C., the reaction mixture is concentrated under reduced pressure. Purification by flash chromatography (silica; methylene chloride/methanol/ammonium hydroxide 98/1/1 to 95/:4/1) gives tert-butyl (1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate (VII, 1.97 g), NMR (300 MHz, MeOH-d4): δ 7.41–6.79, 5.05, 4.33–3.33, 3.74, 3.54, 3.03–2.46 and 1.29; ESI-MS (m/z) [M+H]+=507.

Workup

  1. temperatureUpon cooling to 20–25 degrees C
  2. concentration, the reaction mixture is concentrated under reduced pressure
  3. customPurification by flash chromatography (silica; methylene chloride/methanol/ammonium hydroxide 98/1/1 to 95/:4/1)

Sources & evidence

ORD record
ord-f91046fe2037470b88ac87b8935628f7
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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