Lithium Bromide → HCID 2200539, compound

HRID 85313Notes

Reaction equation

HRID 85313 reaction equation
[BH4-].[Na+].[Li+].[Br-].C([O:7][C:8](=O)[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=1)C>C1COCC1>[CH2:19]([O:18][C:14]1[CH:13]=[C:12]([CH2:11][NH:10][CH2:9][CH2:8][OH:7])[CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 82050Lithium BromideHCID 4311764Sodium borohydrideHCID 59899233HCID 59899233, compound

Product 1

HCID 2200539HCID 2200539, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

Next, NaBH4 (3.8 g, 100 mmol) and LiBr (8.7 g, 100 mmol) were added to THF (100 ml), and the mixture was stirred at 80° C. for 1 hour. To this mixture, [(3-benzyloxyphenyl)methylamino]acetic acid ethyl ester (10.8 g) dissolved in THF (20 ml) was added dropwise at room temperature. The mixture was stirred at 80° C. for 5 hours and further at room temperature for 16 hours. After the reaction solvent was evaporated to about half, KH2PO4 (1 M, 200 ml) was slowly added dropwise. The organic layer was extracted with dichloromethane (50 ml) 3 times, dried over Na2SO4 and concentrated to give crude 2-[(3-benzyloxyphenyl)methylamino]ethanol (yield: 10.3 g (90.4%)).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringThe mixture was stirred at 80° C. for 5 hours and further at room temperature for 16 hours
  3. customAfter the reaction solvent was evaporated to about half, KH2PO4 (1 M, 200 ml)
  4. additionwas slowly added dropwise
  5. extractionThe organic layer was extracted with dichloromethane (50 ml) 3 times
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-84976553f0964cc88e8376c2795ccbc2
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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