tert-Butyl bromoacetate → HCID 86658293, compound

HRID 74856Notes

Reaction equation

HRID 74856 reaction equation
[CH2:1](O)[CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16](CCC[CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[CH3:29][C:30](C)([O-:32])[CH3:31].[K+].Br[CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>C1(C)C=CC=CC=1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:20])[CH:16]([CH2:29][CH:30]([O:32][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:31][CH2:22]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 66603436(6R)-6-[(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-1-ol

Product 1

HCID 86658293HCID 86658293, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Cholestanol (0.662 g, 1.703 mmol) was dissolved in toluene (13 mL). Potassium tert-butoxide (573 mg, 5.11 mmol) was added in one portion. The mixture was stirred at room temperature for 3 hours. tert-Butyl bromoacetate (503 μL, 3.406 mmol) was added drop-wise and the mixture was stirred overnight at room temperature. Toluene (20 mL) was added and the solution was washed with brine (50 mL). The aqueous phase was extracted with toluene (30 mL) before all organic phases were combined, dried (Na2SO4) and the solvent evaporated. The crude product was purified using column chromatography (SiO2; Hexane:EtOAc, 200:1 to 200:20) to yield the white solid product (0.65 g, 76% yield). 1H NMR (400 MHz, CDCl3) δ: 3.98 (s, 2H, CH2O), 3.30 (m, 1H, CHO), 1.97-0.56 (m, 31H), 1.46 (s, 9H, CH3), 0.89 (d, 3H, J=6.1, CH3), 0.85 (d, 3H, J=2.0, CH3), 0.84 (d, 3H, J=1.4, CH3), 0.79 (s, 3H, CH3), 0.64 (s, 3H, CH3).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. washthe solution was washed with brine (50 mL)
  3. extractionThe aqueous phase was extracted with toluene (30 mL) before all organic phases
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-678d897e5d754f00933640dabee675df
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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