Benzyl Alcohol → Benzyl [(1S)-1-(4-methoxyphenyl)ethyl]carbamate

HRID 1755811Notes

Reaction equation

HRID 1755811 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([CH3:13])C(O)=O)=[CH:5][CH:4]=1.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1>[CH2:38]([O:45][C:19]([NH:16][C@H:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH3:13])=[O:28])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 12398859(2S)-2-(4-methoxyphenyl)propanoic acid

Product 1

HCID 57071074Benzyl [(1S)-1-(4-methoxyphenyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of the above acid (28) (29.87 g) in dry toluene (300 mL) at room temperature fitted with a reflux condenser under Ar was added triethylamine (26 mL) followed by diphenylphosphorylazide (38 mL). The reaction was then placed into an oil bath at 80° C. and stirred till gas evolution ceased (~30 min). Benzyl alcohol (17 mL) was next added and the reaction stirred for 3 h at 80° C., evaporated, taken up in ethyl acetate, washed with aqueous 1N Na2CO3, aqueous 1N HCl, saturated NaCl, dried over MgSO4 and evaporated. The product (29) was obtained by flash chromatography on silica gel eluted with 20% ethyl acetate in n-hexane. (42.87 g, 91%): TLC Rf 0.36 (CHCl3) Rf 0.39 (20% ethyl acetate, n-hexane).

Workup

  1. customThe reaction was then placed into an oil bath at 80° C.
  2. custom(~30 min)
  3. stirringthe reaction stirred for 3 h at 80° C.
  4. customevaporated
  5. washwashed with aqueous 1N Na2CO3, aqueous 1N HCl, saturated NaCl
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-fe4bb3f449a74470bee1c35127d5c3cc
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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