Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane → tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate

HRID 1189969Notes

Reaction equation

HRID 1189969 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:9]1[CH:10]=[C:11]([C:15](=[O:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1)[C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)[C:9]1[CH:10]=[C:11]([C@H:15]([OH:26])[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)boraneHCID 68524283Tert-butyl 3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-oxopropylcarbamate

Product 1

HCID 86641455tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-oxopropylcarbamate and (+)-Ipc2BCl in anhydrous THF is stirred at room temperature until no starting material is seen by TLC. The reaction is then quenched with aqueous NH4Cl and stirred at room temperature. Extraction with EtOAc and drying over anhydrous MgSO4 followed by flash chromatography (EtOAc—hexanes gradient) gives tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate.

Workup

  1. customThe reaction is then quenched with aqueous NH4Cl
  2. stirringstirred at room temperature
  3. extractionExtraction with EtOAc
  4. dry with materialdrying over anhydrous MgSO4

Sources & evidence

ORD record
ord-dafcf108c24d41ca90094491f341e634
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

Loading…