Benzyl Alcohol → Benzyl (3-oxocyclobutyl)carbamate

HRID 511608Notes

Reaction equation

HRID 511608 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4](C(O)=O)[CH2:3]1.CC[N:11]([CH:15](C)C)C(C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])=CC=1.[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[O:1]=[C:2]1[CH2:3][CH:4]([NH:11][C:15](=[O:25])[O:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 19794323Benzyl (3-oxocyclobutyl)carbamateYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-oxocyclobutanecarboxylic acid (1.0 g, 8.77 mmol) and DIEA (1.92 g, 14.92 mmol) in toluene (8 mL) was added DPPA (2.89 g, 10.52 mmol) at rt. The mixture was heated to 60° C. under Argon for 3 h, then benzyl alcohol (1.14 g, 10.52 mmol) was added. The mixture was stirred at 60° C. overnight. The reaction was concentrated, the residue was purified by SGC (PE:EA=8:1) to afford the desired compound (240 mg, yield 50%). 1H NMR (500 MHz, CDCl3): δH 7.38-7.33 (m, 5H), 5.12 (d, J=7.5 Hz, 2H), 4.34-4.33 (brs, 1H), 3.44-3.39 (m, 2H), 3.10-3.07 (brs, 2H) ppm; ESI-MS (m/z): 220.2 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by SGC (PE:EA=8:1)

Sources & evidence

ORD record
ord-56bdcebd2c844aebba11c53a4cf5e8a8
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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