Acetic Acid → HCID 89585232, compound

HRID 714764Notes

Reaction equation

HRID 714764 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)=[O:7].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].C(O)(=O)C.[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[OH:7][CH:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:9]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 3611392Lithium tri-s-butylborohydrideHCID 895852361-Piperidinecarboxylic acid, 3-(2-thiazolylcarbonyl)-, 1,1-dimethylethyl ester, (3S)-

Product 1

HCID 89585232HCID 89585232, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, 0.5 g (1.69 mmol) of tert-butyl (S)-3-(thiazole-2-carbonyl)-piperidine-1-carboxylate were dissolved in 20 ml of tetrahydrofuran, and 3.374 ml (3.374 mmol) of lithium tri-sec-butylborohydride (1.0 M solution in tetrahydrofuran) were subsequently added dropwise at room temperature. After 60 minutes, 20 ml of acetic acid (10%) were added. Water, saturated sodium chloride solution and ethyl acetate were then added successively. The organic phase was separated off, the aqueous phase was post-extracted with ethyl acetate, and the combined organic phases were subsequently dried over sodium sulfate, filtered off and evaporated, giving 0.5 g of tert-butyl (S)-3-(hydroxythiazol-2-yl-methyl)piperidine-1-carboxylate as diastereomer mixture of the S-piperidine in the ratio 70:30 (polar:nonpolar); HPLC/MS (M+H)+=299.

Workup

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was post-extracted with ethyl acetate
  3. dry with materialthe combined organic phases were subsequently dried over sodium sulfate
  4. filtrationfiltered off
  5. customevaporated

Sources & evidence

ORD record
ord-9262f4b5b58f43b28333e7e895edbd83
Source dataset
uspto-grants-2015_11
Patent number
US09187469B2

Reaction notes

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