Water → (1R,2S)-2-Amino-1-(3-methoxyphenyl)-1-propanol

HRID 13009Notes

Reaction equation

HRID 13009 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH3:19])[C@H:9]([OH:18])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)(C)(C)C.O.C(O)(C(F)(F)F)=O>ClCCl>[NH2:7][C@@H:8]([CH3:19])[C@@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[OH:18]

Participants

5

Reactant 3

HCID 962Water2×HCID 6422Trifluoroacetic acidHCID 59339845tert-Butyl ((1R,2S)-1-hydroxy-1-(3-methoxyphenyl)propan-2-yl)carbamate

Product 1

HCID 28743837(1R,2S)-2-Amino-1-(3-methoxyphenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl[(1S,2R)-2-hydroxy-2-(3-methoxyphenyl)-1-methylethyl]carbamate (317 mg, 1.13 mmol) in dichloromethane (3 ml) was added water (3 ml), and TFA (5 ml), so that a clear solution has been obtained. The mixture was stirred at r.t. for 1 h, than poured into water (30 ml). The aqueous layer was washed with dichloromethane (30 ml), and made alkaline (pH≈10) by addition of 10 N aqueous NaOH. Brine (20 ml) was added, and the solution was extracted with dichloromethane (3×30 ml). The extracts were dried with Na2SO4, and the solvent was removed under reduced pressure to afford the subtitle compound as colourless oil. Yield 179 mg (88%).

Workup

  1. customso that a clear solution has been obtained
  2. washThe aqueous layer was washed with dichloromethane (30 ml)
  3. additionby addition of 10 N aqueous NaOH
  4. additionBrine (20 ml) was added
  5. extractionthe solution was extracted with dichloromethane (3×30 ml)
  6. dry with materialThe extracts were dried with Na2SO4
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7ddc3f0d016c4cd2b21684b9e6cd7bc8
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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