Boc-Hyp(Bzl)-OH → HCID 14821719, compound

HRID 750020Notes

Reaction equation

HRID 750020 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:21](O)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 11860409Boc-Hyp(Bzl)-OH

Product 1

HCID 14821719HCID 14821719, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

(2S,4R)-4-Benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (960 mg, 3 mmol) in THF (5 mL) was cooled to 0° C. using ice-water bath. Then 1M solution of BH3 (6 mL, 6 mmol) in THF was added under nitrogen over period of 30 min. Reaction was stirred at 0° C. for 2 h and at rt for another 1 h. Reaction mixture was poured over ice water and product was extracted with EtOAc. Organic layers were combined, washed with water, brine, saturated sodium bicarbonate, dried over anhydrous MgSO4 and concentrated to give the crude product. It was used in next step without purification (900 mg, 97%).

Workup

  1. customReaction
  2. customReaction mixture
  3. extractionwas extracted with EtOAc
  4. washwashed with water, brine, saturated sodium bicarbonate
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6bdf0c42d0a44e28953361f68bf2ebe3
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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