Benzyl Alcohol → Benzyl (3-oxocyclobutyl)carbamate

HRID 511608

反応式

HRID 511608 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 19794323Benzyl (3-oxocyclobutyl)carbamate収率 50%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-56bdcebd2c844aebba11c53a4cf5e8a8
出典データセット
uspto-grants-2015_08
特許番号
US09096634B2

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