1-Phenethylamine, (-)- → (5RS,6SR)-2,2-dimethyl-6-{[(1S)-1-phenylethyl]amino}-1,3-dioxepan-5-ol

HRID 390077Notes

Reaction equation

HRID 390077 reaction equation
[C:1]1([C@@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][C:11]1([CH3:19])[O:18][CH2:17][CH:16]2[CH:14]([O:15]2)[CH2:13][O:12]1>CC(O)C>[CH3:10][C:11]1([CH3:19])[O:18][CH2:17][C@@H:16]([OH:15])[C@H:14]([NH:9][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[CH2:13][O:12]1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

Product 1

HCID 58158434(5RS,6SR)-2,2-dimethyl-6-{[(1S)-1-phenylethyl]amino}-1,3-dioxepan-5-olYield 35%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The known method by T. Inaba, A. G. Birchler, Y. Yamada, S. Sagawa, K. Yokata, K. Ando and I. Uchida, J. Org. Chem., 1998, 63, 7582 for the preparation of the enantiomer of the title compound was followed. (S)-1-Phenylethanamine (30.4 ml, 236 mmol) and 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane (34 g, 236 mmol) were dissolved in iPrOH (16 ml) and heated under reflux for 16 h. The mixture was stirred and cooled in an ice bath. Hexanes (90 ml) was added. After 1 h the colourless crystalline solid was filtered off, washed with hexanes and dried to give (5S,6R)-2,2-dimethyl-6-((S)-1-phenylethylamino)-1,3-dioxepan-5-ol (21.9 g, 35%). The 1H NMR was in agreement with that described for the enantiomer of the title compound by T. Inaba, A. G. Birchler, Y. Yamada, S. Sagawa, K. Yokata, K. Ando and I. Uchida, J. Org. Chem., 1998, 63, 7582. [α]D 20 −96.6 (c, 1.01, MeOH). Lit. (T. Inaba, A. G. Birchler, Y. Yamada, S. Sagawa, K. Yokata, K. Ando and I. Uchida, J. Org. Chem., 1998, 63, 7582) [α]D 25 +96.2 (c 1.00, MeOH) for the enantiomer.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. temperaturecooled in an ice bath
  4. filtrationAfter 1 h the colourless crystalline solid was filtered off
  5. washwashed with hexanes
  6. customdried

Sources & evidence

ORD record
ord-c62eee8ce7ae4b2c92487104475b014d
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

Loading…