Water → HCID 118006534, compound

HRID 1486796Notes

Reaction equation

HRID 1486796 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][C@H:7]([CH3:9])[CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:9][C@H:7]1[CH2:8][C@@H:3]([CH2:2][O:1][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH2:4][N:5]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 118006982(3R,5S)-tert-butyl 3-(hydroxymethyl)-5-methylpiperidine-1-carboxylate

Product 1

HCID 118006534HCID 118006534, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3R,5S)-tert-butyl 3-(hydroxymethyl)-5-methylpiperidine-1-carboxylate (0.783 g, 3.385 mmol) in DCM (5 mL) was added p-toluenesulfonyl chloride (0.968 g, 5.078 mmol) followed by DMAP (40 mg, 0.33 mmol) and DIPEA (1.18 mL, 6.77 mmol) at rt. The reaction mixture was stirred at rt for 3 h after which time water (5 mL) was added followed by stifling an additional 15 min. The resultant organic layer was washed with 0.1 N HCl (5 mL), brine (3 mL), dried over MgSO4, filtered and concentrated to dryness. The crude product was purified over silica gel (Biotage, eluting with 3:1 heptanes: EtOAc) to provide (3S,5R)-tert-butyl 3-methyl-5-((tosyloxy)methyl)piperidine-1-carboxylate (0.8602 g, 2.232 mmol, 65.9% yield).

Workup

  1. additionwas added
  2. washThe resultant organic layer was washed with 0.1 N HCl (5 mL), brine (3 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified over silica gel (Biotage, eluting with 3:1 heptanes: EtOAc)

Sources & evidence

ORD record
ord-34179b7aa953480ab85289f485a5c159
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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