Iodobenzene diacetate → Benzyl (3-Oxopropyl)carbamate

HRID 606614Notes

Reaction equation

HRID 606614 reaction equation
[CH2:1]([O:8][C:9](=[O:15])[NH:10][CH2:11][CH2:12][CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)N([O])C(C)(C)CCC1.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:15])[NH:10][CH2:11][CH2:12][CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 76724Iodobenzene diacetate2×HCID 562256Benzyl N-(3-hydroxypropyl)carbamateHCID 2724126Tempo

Product 1

HCID 10398106Benzyl (3-Oxopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3-hydroxy-propyl)-carbamic acid benzyl ester (100 g, 478 mmol) and 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical (TEMPO; 7.5 g, 48 mmol) in DCM (1 L) was treated with (diacetoxyiodo)benzene, PhI(OAc)2, (170 g, 528 mmol) in three portions. After 18 h at rt, the mixture was slowly quenched with saturated aqueous (satd. aq.) NaHCO3. The organic layer was separated, washed with satd. aq. NaCl (500 mL), dried (Na2SO4), and concentrated. The residue was purified by FCC to give a solid, which was stirred in 1:1 Et2O/hexanes for 2 h. The solid was collected by filtration. Successive iterations were combined to provide the title compound as a white solid. 1H NMR (400 MHz, CDCl3): 9.81 (s, 1H), 7.36-7.31 (m, 5H), 5.14 (br s, 1H), 5.08 (s, 2H), 3.49 (q, J=6.0, 2H), 2.75 (t, J=5.7, 2H).

Workup

  1. customthe mixture was slowly quenched with saturated aqueous (satd. aq.) NaHCO3
  2. customThe organic layer was separated
  3. washwashed with satd
  4. dry with materialaq. NaCl (500 mL), dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by FCC
  7. customto give a solid, which
  8. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-e7be2534e4f04920b6d9439d0284a44a
Source dataset
uspto-grants-2011_03
Patent number
US07915404B2

Reaction notes

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