Sodium Carbonate → HCID 69118652, compound

HRID 1375621Notes

Reaction equation

HRID 1375621 reaction equation
[CH3:1][C:2]1([CH3:19])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([C@@H:14]([CH2:16][CH:17]=O)[CH3:15])[CH2:4][O:3]1.C(N1CCC(N)CC1)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[C:50](Cl)([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51]>C1COCC1.O>[CH2:53]([O:52][C:50]([CH2:17][CH2:16][C@H:14]([C@H:5]1[CH2:4][O:3][C:2]([CH3:19])([CH3:1])[N:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:15])=[O:51])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 31633331-(Propan-2-yl)piperidin-4-amineHCID 5049666Sodium triacetoxyborohydrideHCID 11300233HCID 11300233, compound

Product 1

HCID 69118652HCID 69118652, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the product from Step c dissolved in THF (20 mL) was added 1-isopropylpiperidin-4-amine (0.5 mL, excess) followed by the addition of sodium triacetoxyborohydride (0.85 g, 4.02 mmol). The mixture was stirred at rt. over night. Into the same pot mixture were added water (6.0 mL), sodium carbonate (0.5 g), and CBZCl (0.5 mL). The mixture was stirred at rt. for 2 hr. The mixture was extracted with ethyl acetate. Organic phase was washed with sodium bicarbonate and brine and dried over sodium sulfate. The product, (S)-tert-butyl 4-((R)-4-(benzyloxycarbonyl)butan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate, was obtained after reverse phase HPLC purification (acetonitrile/water 30% to 100% gradient). LC-MS found: (M+1)+=532.47.

Workup

  1. waitover night
  2. stirringThe mixture was stirred at rt
  3. extractionThe mixture was extracted with ethyl acetate
  4. washOrganic phase was washed with sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-6fc9736c0e934756a2c6e7e713ddbcd2
Source dataset
uspto-grants-2007_01
Patent number
US07169795B2

Reaction notes

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