tert-Butanol → HCID 58430865, compound

HRID 1040488Notes

Reaction equation

HRID 1040488 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1(C(O)=O)[CH2:10][CH2:9][CH2:8]1.CC[N:16]([CH2:19]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[CH3:38][C:39]([OH:42])([CH3:41])[CH3:40]>>[C:39]([O:42][C:19](=[O:28])[NH:16][C:7]1([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:8][CH2:9][CH2:10]1)([CH3:41])([CH3:40])[CH3:38]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 532566591-(Pyridin-2-yl)cyclobutane-1-carboxylic acid

Product 1

HCID 58430865HCID 58430865, compound

Procedure

1-Pyridin-2-yl-cyclobutanecarboxylic acid (2.0 g, 11.3 mmol) was combined with t-BuOH 50 mL), Et3N (1.78 mL, 12.4 mmol) and diphenylphosphoryl azide (2.7 mL, 12.4 mmol). The reaction was heated to reflux for 1.5 h. The t-BuOH was removed in vacuo to yield 7.0 g of crude (1-pyridin-2-yl-cyclobutyl)-carbamic acid tert-butyl ester as a pink-black oil. The crude product was used in subsequent reactions without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1.5 h
  3. customThe t-BuOH was removed in vacuo

Sources & evidence

ORD record
ord-c0d0629e4bb1470f99b341d9d032b5b8
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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