Acetic Acid → ((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride

HRID 1011963Notes

Reaction equation

HRID 1011963 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[NH:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][OH:21].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:41]>Cl.O1CCOCC1>[ClH:41].[ClH:41].[NH:8]1[CH2:9][CH2:10][CH:11]([N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[CH2:20][OH:21])[CH2:12][CH2:13]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 90908ProlinolHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66901571((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 5 mmol), S)-1-pyrrolidin-2-yl-methanol (0.6 g, 6 mmol), acetic acid (0.3 ml, 6 mmol) in CH2Cl2 (10 ml) was added sodium triacetoxyborohydride (1.2 g, 6 mmol). The reaction was stirred for 1 h after which time it was washed with saturated sodium hydrogen carbonate, dried with sodium sulphate and concentrated. The residue (1.1 g, 4 mmol) was redissolved in 4M hydrochloric acid in dioxane (6 ml) and stirred for 1 h. Concentration afforded the title compound (1.0 g, quant) as a light orange foam. MS: 185.1 (MH+).

Workup

  1. washwas washed with saturated sodium hydrogen carbonate
  2. dry with materialdried with sodium sulphate
  3. concentrationconcentrated
  4. stirringstirred for 1 h
  5. concentrationConcentration

Sources & evidence

ORD record
ord-131c668c87fd42418143c6a46b31076f
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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