tert-butyl N-(2-oxoethyl)carbamate → HCID 86612293, compound

HRID 2074426Notes

Reaction equation

HRID 2074426 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][C@@H:6]([CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[O:7][C@H:8]2[CH2:14][NH:15][CH:16]=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[CH:39][CH2:40][NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45]>ClC(Cl)C>[C:44]([O:43][C:42](=[O:48])[NH:41][CH2:40][CH2:39][N:21]1[CH2:20][CH2:19][CH:18]([C@@H:6]2[CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:12]([CH3:13])[C:3]=3[O:2][CH3:1])[C@H:8]([CH2:14][NH:15][CH:16]=[O:17])[O:7]2)[CH2:23][CH2:22]1)([CH3:47])([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 4247255tert-butyl N-(2-oxoethyl)carbamate2×HCID 5049666Sodium triacetoxyborohydrideHCID 11695413HCID 11695413, compound

Product 1

HCID 86612293HCID 86612293, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent3×

Procedure

Stir a solution of N-((1R,3S)-5-methoxy-6-methyl-3-(4-piperidinyl)-1-isochromanyl-methyl)formamide (4.0 g, 12.5 mmole) in dichloroethane (110 mL) and add sodium triacetoxyborohydride (4.0 g, 18.8 mmole). Dissolve t-butyl N-(2-oxoethyl)-carbamate (1.0 g, 6.3 mmole) in dichloroethane (20 mL) and add it to the reaction mixture. After 6 hours add another 6.3 mmole of t-butyl N-(2-oxoethyl)-carbamate in dichloroethane. After another 42 hours adjust the pH of the reaction mixture to about 14 with 50% NaOH and extract with dichloromethane. Wash the combined extracts with water and dry over Mg2SO4. Purify the crude product on a 33 g silica gel column (eluting with ammonium hydroxide:methanol:ethyl acetate 1:1:98). Collect the appropriate fractions and concentrate to obtain the title compound. CIMS 462, tR (min)=0.46.

Workup

  1. extractionthe pH of the reaction mixture to about 14 with 50% NaOH and extract with dichloromethane
  2. washWash the combined extracts with water
  3. dry with materialdry over Mg2SO4
  4. customPurify the crude product
  5. washon a 33 g silica gel column (eluting with ammonium hydroxide:methanol:ethyl acetate 1:1:98)
  6. customCollect the appropriate fractions
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-d1be70df43c1411c900d1a277f347180
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

Loading…