1-Propanol → HCID 86718382, compound

HRID 1518768Notes

Reaction equation

HRID 1518768 reaction equation
[C:1](=[O:11])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:2].[OH-:12].[Na+].Cl[O:15][C:16]([CH3:19])(C)C.[CH3:20][O:21][C:22]1[CH:33]=[CH:32][C:25](C=CC(OC)=O)=[CH:24][CH:23]=1.[CH2:34]([OH:37])[CH2:35][CH3:36]>O.CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1>[CH2:4]([O:3][C:1]([NH:2][C@H:36]([C:25]1[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:33][CH:32]=1)[C@H:35]([OH:12])[C:34]([O:15][CH2:16][CH3:19])=[O:37])=[O:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 10311-Propanol2×HCID 12136Benzyl carbamateHCID 14798Sodium HydroxideHCID 928414-Methoxycinnamate methyl esterHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 86718382HCID 86718382, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 112172021,4-Bis(dihydroquinidine)phthalazineCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl carbamate (4.89 g, 32 mmol, 2.3 equiv) was dissolved in 24 mL of n-PrOH. A solution of NaOH (1.3 g, 32 mmol, 2.3 equiv) in 36 mL of H2O was added to this stirred solution and the mixture was cooled at 0° C. in an ice water bath. To the mixture was then added tert-butyl hypochlorite (3.5 g, 32 mmol, 2.3 mmol). After stirring at 0° C. for 10 minutes, (DHQD)2PHAL (0.55 g, 0.7 mmol, 0.05 equiv) and 12 mL of n-PrOH was added. The reaction flask was immersed in a room-temperature water bath and stirred for 5 minutes. Methyl 4-methoxycinnamate (2.9 g, 14 mmol, 1.0 equiv) was added, followed by K2OsO2(OH)4 (207 mg, 0.56 mmol, 0.04 equiv). The reaction mixture was stirred for 2 hour at 0° C. by which it transformed into a pale yellow slurry. The precipitate was isolated by filtration. One wash with ice-cold EtOH—H2O (1:1, 5 mL) yielded product 2.21.1a as a white solid (3.5 g, 67%, >99% ee). MS m/z (M+Na+) 396

Workup

  1. customThe reaction flask was immersed in a room-temperature water bath
  2. stirringstirred for 5 minutes
  3. stirringThe reaction mixture was stirred for 2 hour at 0° C. by which it
  4. customThe precipitate was isolated by filtration
  5. washOne wash with ice-cold EtOH—H2O (1:1, 5 mL)

Sources & evidence

ORD record
ord-6fc3303e64a649d1b37d4330f95bbbb3
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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