Propargyl bromide → HCID 25178773, compound

HRID 1852330Notes

Reaction equation

HRID 1852330 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[CH2:17](Br)[C:18]#[CH:19]>CN(C=O)C>[CH2:19]([O:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:18]#[CH:17]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 14797Potassium HydroxideHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 25178773HCID 25178773, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 18 (0.40 g, 2 mmol) in dry DMF (10 mL) was added potassium hydroxide (0.56 g, 10 mmol), followed by dropwise addition of propargyl bromide (80 wt. % in toluene) (0.48 g, 4 mmol) over 5 min. After 18 h the reaction mixture was poured onto water (30 mL) and washed with DCM (3×15 mL). The combined organic fractions concentrated in vacuo and the liquid remaining taken up in diethyl ether (15 mL) and washed with water (2×10 mL), then brine (1×10 mL) and dried over Na2SO4. Chromatography (hexanes/ethyl acetate) gave the desired product as a colorless oil (0.32 g, 67%). HRMS (ESI)=240.1597 (M+H)+. Calcd. for C13H22NO3 240.1594. 1H NMR (600 MHz, CDCl3) δ 4.13 (s, 2H), 3.96-3.88 (m, 1H), 3.64 (dd, J=9 Hz, J=3.6 Hz, 1H), 3.49-3.22 (m, 3H), 2.40 (s, 1H), 1.94-1.78 (m, 4H), 1.46 (s, 9H). TLC (I2) Rf=0.67 (1:1 hexanes/ethyl acetate).

Workup

  1. additionAfter 18 h the reaction mixture was poured onto water (30 mL)
  2. washwashed with DCM (3×15 mL)
  3. concentrationThe combined organic fractions concentrated in vacuo
  4. washwashed with water (2×10 mL)
  5. dry with materialbrine (1×10 mL) and dried over Na2SO4

Sources & evidence

ORD record
ord-6cb816d6ea824037b55c9fb848f93691
Source dataset
uspto-grants-2015_02
Patent number
US08961930B2

Reaction notes

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