Benzyl Alcohol → Benzyl (3-oxocyclobutyl)carbamate

HRID 511608노트

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HRID 511608 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 19794323Benzyl (3-oxocyclobutyl)carbamate수율 50%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
60 °C

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-56bdcebd2c844aebba11c53a4cf5e8a8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096634B2

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