Hydrochloric Acid → HCID 22851794, compound

HRID 1034499Notes

Reaction equation

HRID 1034499 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:12]2[C:13](O)=[O:14])=[O:10])=[CH:5][CH:4]=1.ClC(OCC)=O.[BH4-].[Na+].Cl>O1CCCC1.C(N(CC)CC)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:12]2[CH2:13][OH:14])=[O:10])=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 15671477HCID 15671477, compound

Product 1

HCID 22851794HCID 22851794, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of trans-1-p-methoxybenzyloxycarbonyl-4-hydroxyproline (105.5 g: 357.5 mmole) in tetrahydrofuran (1 liter), triethylamine (54.8 ml) is added. After adding ethyl chloroformate (35.9 ml) dropwise at -30° C., the mixture is stirred for 20 minutes. To the reaction mixture, a solution of sodium borohydride (33.25 g) in water (120 ml) is added dropwise at a temperature in the range of -15° to -5° C., neutralized with conc. hydrochloric acid, and concentrated in vacuo. To the residue, ethyl acetate is added, washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxy-pyrrolidine-2-methanol. NMR δ(CDCl3) ppm: 1.6 to 1.8(m, 1H), 1.95 to 2.2(m, 1H), 3.4 to 3.8 (m, 4H), 3.8(s, 3H), 4.0 to 4.3(m, 1H), 4.37(br s, 1H), 5.07(s, 2H), 6.88(d, J=8.8 Hz, 2H), 7.30(d, J=8.8 Hz, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue, ethyl acetate is added
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62e4a58ef0bb48928a8b7a80318160f8
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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