Tributylphosphine → HCID 86697211, compound

HRID 237546Notes

Reaction equation

HRID 237546 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[Br:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH2:25][CH2:26]O)=[CH:20][C:19]=1[CH3:28].[C:29]([O:33][C:34]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:35])([CH3:32])([CH3:31])[CH3:30].C(P(CCCC)CCCC)CCC>ClCCl>[C:40]([O:39][C:37]([N:36]([C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])[CH2:26][CH2:25][C:21]1[CH:22]=[C:23]([CH3:24])[C:18]([Br:17])=[C:19]([CH3:28])[CH:20]=1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 279800Di-tert-butyl IminodicarboxylateHCID 89808620HCID 89808620, compound

Product 1

HCID 86697211HCID 86697211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of di-tert.-butyl azodicarboxylate (2.85 g) in dichloromethane (10 mL) is added dropwise over 15 minutes to a solution of 2-(4-bromo-3,5-dimethylphenyl)ethanol (950 mg), di-tert.butyl-iminodicarboxylate (3.75 g) and tributylphosphine (4.4 mL) in dichloromethane (40 mL) at −10° C. The resulting solution is stirred for 2 hours while warming to room temperature and then partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The aqueous phase is extracted with dichloromethane. The combined organic phases are dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. Yield: 1.19 g; LC (method 8): tR=1.06 min; Mass spectrum (ESI+): m/z=451 [M+Na]+.

Workup

  1. custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record
ord-75f7531895be431bb9e5b6019860be1e
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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