tert-Butanol → Tert-butyl (1-(5-iodopyridin-2-YL)cyclobutyl)carbamate

HRID 2038757Notes

Reaction equation

HRID 2038757 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2(C(O)=O)[CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:15]([OH:19])([CH3:18])([CH3:17])[CH3:16].CC[N:22]([CH2:25]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])=CC=1>>[C:15]([O:19][C:25](=[O:34])[NH:22][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][N:6]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 675084441-(5-Iodopyridin-2-YL)cyclobutanecarboxylic acid

Product 1

HCID 67509277Tert-butyl (1-(5-iodopyridin-2-YL)cyclobutyl)carbamateYield 22.8%

Conditions

Temperature
85 °C

Procedure

1-(5-Iodo-pyridin-2-yl)-cyclobutane carboxylic acid (3.92 g, 12.9 mmol) was combined with tert-BuOH (6.1 mL, 65 mmol), Et3N (9.0 mL, 65 mmol) and DPPA (3.1 mL, 14 mmol). The reaction was heated to reflux (external bath: 85° C.) for 1.5 h. The volatiles were removed in vacuo and the crude reaction mixture was purified by normal phase flash chromatography on silica gel (5→80% EtOAc/hexanes) to give 1.1 g of [1-(5-iodo-pyridin-2-yl)-cyclobutyl]-carbamic acid tert-butyl ester as a solid, m/z 375.4 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. customThe volatiles were removed in vacuo
  3. customthe crude reaction mixture
  4. customwas purified by normal phase flash chromatography on silica gel (5→80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c546a4b2cd4b401f83ef17c80866eb45
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

Loading…