Isopropyl chloroformate → HCID 70856319, compound

HRID 1850757Notes

Reaction equation

HRID 1850757 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[NH:8]1[CH2:13][CH2:12][CH:11]([C@H:14]2[CH2:16][C@H:15]2[CH2:17][CH2:18][OH:19])[CH2:10][CH2:9]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[OH:19][CH2:18][CH2:17][C@@H:15]1[CH2:16][C@@H:14]1[CH:11]1[CH2:10][CH2:9][N:8]([C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 10796Cesium carbonateHCID 867111782-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol

Product 1

HCID 70856319HCID 70856319, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Isopropyl chloroformate (0.12 μL, 1.0 mmol) was added dropwise to a solution of 2-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol (170 mg, 1.0 mmol) and cesium carbonate (650 mg, 2.0 mmol) in acetonitrile (5 mL). After total addition, the mixture was stirred for 2 hours at RT. The solution was concentrated under reduced pressure and the residue taken-up in 10 mL DCM. The solution was washed with water, the organics were collected, dried over sodium sulfate, filtered and the filtrate concentrated to dryness under reduced pressure. The residue by flash chromatography (20 g of silica gel, ISCO, eluted with a gradient 0-100% ethyl acetate in Hexane) to afford the title compound (189 mg, 74%). LC/MS 256 (M+H)+.

Workup

  1. additionAfter total addition
  2. concentrationThe solution was concentrated under reduced pressure
  3. washThe solution was washed with water
  4. customthe organics were collected
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated to dryness under reduced pressure
  8. washThe residue by flash chromatography (20 g of silica gel, ISCO, eluted with a gradient 0-100% ethyl acetate in Hexane)

Sources & evidence

ORD record
ord-4c4842c428c04cb6bdcab76a402b8a72
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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