Imidazole → HCID 22220462, compound

HRID 655113Notes

Reaction equation

HRID 655113 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:9]([N:22]1[CH2:25][CH:24]([OH:26])[CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CN=C1>C(Cl)Cl>[CH:9]([N:22]1[CH2:25][CH:24]([O:26][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 22220462HCID 22220462, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyldimethylsilyl chloride (1.524 g, 10.11 mmol) was added to 1-benzhydrylazetidin-3-ol (CAS no. 18621-17-5) (2.2 g, 9.19 mmol) and imidazole (1.565 g, 22.98 mmol) in DCM (46.0 mL) at r.t. under nitrogen. The resulting solution was stirred at r.t. for 3 hours. The reaction mixture was quenched with water, poured onto a phase separator and evaporated to afford the product (3.66 g, 113%). 1H NMR (400 MHz, CDCl3) δ 0.00 (6H, s), 0.85 (9H, s), 2.81 (2H, s), 3.52 (2H, s), 4.35 (1H, s), 4.40-4.49 (1H, m), 7.08-7.43 (10H, m); m/z (ES+) (M+H)+=354.55; HPLC tR=2.04 min.

Workup

  1. customat r.t.
  2. customThe reaction mixture was quenched with water
  3. additionpoured onto a phase separator
  4. customevaporated

Sources & evidence

ORD record
ord-e9b5d1c8fa2f4f39b791aafb805c59d5
Source dataset
uspto-grants-2011_12
Patent number
US08071585B2

Reaction notes

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