Sodium borohydride → HCID 59563691, compound

HRID 1944149Notes

Reaction equation

HRID 1944149 reaction equation
[C:1]([CH:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[BH4-].[Na+]>C1COCC1>[NH2:2][CH2:1][CH:3]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][O:16][Si:17]([CH:24]([CH3:25])[CH3:26])([CH:18]([CH3:20])[CH3:19])[CH:21]([CH3:22])[CH3:23])=[CH:13][CH:14]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59563706HCID 59563706, compound

Product 1

HCID 59563691HCID 59563691, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of CoCl2.6H2O in THF was added ethyl 2-cyano-2-(4-((triisopropylsilyloxy)methyl)phenyl)acetate (E200). The mixture was cooled to 0° C. and NaBH4 was added to the mixture in several portions over 30 min. The mixture was stirred at room temperature for 4 h. The reaction was quenched with water. The mixture was filtered and the filtrate extracted twice with ether. The organics were dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, DCM:EtOH=50:1) gave pure ethyl 3-amino-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoate (E201) as a yellow oil.

Workup

  1. customThe reaction was quenched with water
  2. filtrationThe mixture was filtered
  3. extractionthe filtrate extracted twice with ether
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0b44c41ec18e4e4f86298d1e2b2de6aa
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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