HCID 178418361, compound → HCID 178476816, compound

HRID 1062533Notes

Reaction equation

HRID 1062533 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][PH:18](=[O:22])[O:19][CH2:20][CH3:21])[CH2:10]1)(C(C)(C)C)(C)C.[H][H]>O=[Pt]=O>[OH:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][PH:18](=[O:22])[O:19][CH2:20][CH3:21])[CH2:10]1

Participants

4

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178476817HCID 178476817, compound

Product 1

HCID 178476816HCID 178476816, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

A related strategy was applied to the synthesis of (±)-(cis-3-aminocyclopentanyl)methylphosphinic acid (Scheme 3). However, in this synthesis, a Mitzanobu reaction was performed at the start of the sequence on isopropyl (±)-(3-hydroxycyclopentenyl)methylphosphinate (3) to yield (±)-isopropyl (3-aminocyclopentenyl)methylphosphinate (8). The amine was then protected as the t-butyloxycarbonylamide (BOC) (9) which provided the steric bulk to direct the approach of the hydrogen. The hydrogenation was carried out over PtO2 at 40 psi affording the (±)-cis-N-butyloxycarbonyl cyclopentane (10) in quantitative yield and a diastereomeric excess of 95:5 cis:trans. The minor diastereoisomer could be separated by silica gel chromatography.

Workup

  1. customprovided the steric bulk

Sources & evidence

ORD record
ord-e5084591389c4712b453289eeb6abdbb
Source dataset
uspto-grants-2005_11
Patent number
US06962907B2

Reaction notes

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