Heptane → HCID 86635761, compound

HRID 1879809Notes

Reaction equation

HRID 1879809 reaction equation
[C:1]([O:4][CH2:5][C:6](=O)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].Cl.[CH3:14][NH:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CCCCCCC>ClC(Cl)C.CCOC(C)=O>[C:9]([O:8][CH2:7][CH:6]([N:15]([CH3:14])[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 8900HeptaneHCID 2434181,3-DiacetoxyacetoneHCID 5049666Sodium triacetoxyborohydrideHCID 11252350Sarcosine t-butyl ester hydrochloride

Product 1

HCID 86635761HCID 86635761, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(acetyloxy)-2-oxopropyl acetate (4.54 g, 26 mmol) in dichloroethane (75 ml) was added tert-butyl 2-(methylamino)acetate HCl. After stirring for 10 minutes sodium triacetoxyborohydride (8.3 g, 39 mmol) was added and stirring was continued for 18 hours and monitored by TLC (1:1 heptane:EtOAc). The reaction was quenched by the addition of saturated sodium hydrogen carbonate solution and the crude product was extracted into dichloromethane. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. The title compound was purified by silica column chromatography eluting with 0-20% EtOAc:Hept to yield the title compound (1.32 g, 17% yield). 1H NMR (250 MHz, CHLOROFORM-d) δ 4.07-4.33 (4H, m), 3.34 (2H, s), 3.23 (1H, t, 5.9 Hz), 2.49 (3H, s), 1.99-2.19 (6H, m), 1.33-1.55 (9H, m).

Workup

  1. additionwas added
  2. customThe reaction was quenched by the addition of saturated sodium hydrogen carbonate solution
  3. extractionthe crude product was extracted into dichloromethane
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe title compound was purified by silica column chromatography
  9. washeluting with 0-20% EtOAc

Sources & evidence

ORD record
ord-c6e9f58a9e064437b3d7833d5cc2ecd2
Source dataset
uspto-grants-2012_11
Patent number
US08318705B2

Reaction notes

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