Hydrochloric Acid → (2R,3S)-3-amino-4-phenyl-1-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)butan-2-ol hydrochloride

HRID 387622Notes

Reaction equation

HRID 387622 reaction equation
[CH2:1]([C@H:8]([NH:26]C(=O)OC(C)(C)C)[C@H:9]([OH:25])[CH2:10][NH:11][C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:34]>ClCCl.O1CCOCC1>[ClH:34].[NH2:26][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]([OH:25])[CH2:10][NH:11][C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86644019tert-butyl[(1S,2R)-1-benzyl-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]carbamate

Product 1

HCID 68473826(2R,3S)-3-amino-4-phenyl-1-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)butan-2-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

6.8 g of tert-butyl [(1S,2R)-1-benzyl-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]carbamate are then dissolved in 250 cm3 of dichloromethane at a temperature close to 20° C. 36.6 cm3 of a 4M solution of hydrochloric acid in dioxane are added. The reaction mixture is kept stirring for 1 h 30 min at a temperature close to 20° C. The reaction mixture is concentrated using a rotary evaporator under reduced pressure (5 kPa). The beige solid obtained is triturated in diisopropyl ether then filtered. 5.4 g of (2R,3S)-3-amino-4-phenyl-1-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)butan-2-ol hydrochloride (2:1) are obtained.

Workup

  1. customclose to 20° C
  2. customclose to 20° C
  3. concentrationThe reaction mixture is concentrated
  4. customa rotary evaporator under reduced pressure (5 kPa)
  5. customThe beige solid obtained
  6. customis triturated in diisopropyl ether
  7. filtrationthen filtered

Sources & evidence

ORD record
ord-8bf47fd7e8b94cefac2065913897bd49
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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