Benzyl Alcohol → Benzyl (3-oxocyclobutyl)carbamate

HRID 2040648Notes

Reaction equation

HRID 2040648 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, 1 H), 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-bbf2f5c9d9b24d9a8079896f04c76be3
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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