Sodium borohydride → HCID 21069257, compound

HRID 1244172Notes

Reaction equation

HRID 1244172 reaction equation
[C:1]([O:5][C:6]([C:8]1([S:14]([N:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)(=[O:16])=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([C:8]1([S:14]([N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)(=[O:16])=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21931280HCID 21931280, compound

Product 1

HCID 21069257HCID 21069257, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 250 mL round-bottom flask was charged with 4-(4-oxo-piperidine-1-sulfonyl)-tetrahydro-pyran-4-carboxylic acid tert-butyl ester (10 g, 29 mmol) and methanol (100 mL). The resulting slurry was rapidly stirred with an overhead-stirring paddle, and the flask was immersed into an ice bath. Sodium borohydride (1.09 g, 29 mmol) was added in three portions over 15 min. After complete addition, the homogeneous mixture was warmed to room temperature and stirred for 30 min. The flask was again immersed into an ice water bath, and the reaction was quenched by careful addition of a saturated ammonium chloride solution (25 mL). The mixture was then warmed to room temperature, diluted with water (100 mL), and extracted with methylene chloride (3×100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. This afforded 10 g of an off-white, crystalline solid (99% yield). 1H NMR (CDCl3) δ 1.50 (s, 9H), 1.53–1.62 (m, 2H), 1.68 (br s, 1H), 1.86–1.92 (m, 2H), 2.11 (td, J=4.7, 12.8 Hz, 2H), 2.30 (d, J=11.2 Hz, 2H), 3.17 (m, 2H), 3.29 (t, J=12.2 Hz, 2H), 3.63 (m, 2H), 385 (m, 1H), 3.94 (dd, J=4, 11.2 Hz, 2H); Electrospray mass spectrometry showed m/z=350 (M+H)+.

Workup

  1. customthe flask was immersed into an ice bath
  2. additionAfter complete addition
  3. stirringstirred for 30 min
  4. customThe flask was again immersed into an ice water bath
  5. customthe reaction was quenched by careful addition of a saturated ammonium chloride solution (25 mL)
  6. temperatureThe mixture was then warmed to room temperature
  7. additiondiluted with water (100 mL)
  8. extractionextracted with methylene chloride (3×100 mL)
  9. dry with materialThe combined organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1be178612aaf4dcca19e025425f54bfa
Source dataset
uspto-grants-2006_10
Patent number
US07119203B2

Reaction notes

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